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Volumn 2015, Issue 10, 2015, Pages 2197-2204

Radical Decarboxylative Fluorination of Aryloxyacetic Acids Using N-Fluorobenzenesulfonimide and a Photosensitizer

Author keywords

Fluorine; Photochemistry; Photosensitizer; Radicals

Indexed keywords


EID: 85027919745     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201500038     Document Type: Article
Times cited : (41)

References (59)
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    • For reviews, see:
    • For reviews, see:.
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    • see ref.[1]
    • see ref.[1].
  • 10
    • 85130089752 scopus 로고    scopus 로고
    • For recent examples of ionic and cross-coupling methods, see:
    • For recent examples of ionic and cross-coupling methods, see:.
  • 18
    • 85130082349 scopus 로고    scopus 로고
    • For recent examples of carbene-mediated methods see:
    • For recent examples of carbene-mediated methods see:.
  • 31
    • 0029045460 scopus 로고
    • Tius, M.A., Tetrahedron 51 (1995), 6605–6634.
    • (1995) Tetrahedron , vol.51 , pp. 6605-6634
    • Tius, M.A.1
  • 39
    • 85130089247 scopus 로고    scopus 로고
    • There are multiple conflicting reports for the reduction potential of both Selectfluor and NFSI. We selected the most recently reported values (see ref.[16]). See also:
    • There are multiple conflicting reports for the reduction potential of both Selectfluor and NFSI. We selected the most recently reported values (see ref.[16]). See also:.
  • 43
  • 44
    • 85130084224 scopus 로고    scopus 로고
    • NFSI absorbs at 270 nm with a shoulder at 277 nm. For an absorbance spectrum, see the Supporting Information.
    • NFSI absorbs at 270 nm with a shoulder at 277 nm. For an absorbance spectrum, see the Supporting Information.
  • 45
    • 85130083376 scopus 로고    scopus 로고
    • The absorption maxima for acetone occurs at 270 nm and tails to 330 nm. See: Tables of Physical & Chemical Constants, 16th ed., 1995, chapter 3.8.7. Kaye & Laby Online, version 1.0 (retrieved April 15, 2013).
    • The absorption maxima for acetone occurs at 270 nm and tails to 330 nm. See: Tables of Physical & Chemical Constants, 16th ed., 1995, chapter 3.8.7. Kaye & Laby Online, version 1.0, 2005: www.kayelaby.npl.co.uk (retrieved April 15, 2013).
    • (2005)
  • 46
    • 85130084946 scopus 로고    scopus 로고
    • With the exception of substrate 1g, which was originally reported in a previous Selectfluor reactivity study (ref.[8]), all compounds are new. See the Supporting Information for experimental details.
    • With the exception of substrate 1g, which was originally reported in a previous Selectfluor reactivity study (ref.[8]), all compounds are new. See the Supporting Information for experimental details.
  • 47
    • 85130089544 scopus 로고    scopus 로고
    • Substrates 2g, 2h, and 2i could be synthesized by using our photoredox catalysis method (ref.[9]) owing to the lower energy light that was utilized.
    • Substrates 2g, 2h, and 2i could be synthesized by using our photoredox catalysis method (ref.[9]) owing to the lower energy light that was utilized.
  • 48
    • 85130083414 scopus 로고    scopus 로고
    • The remaining mass balance contained fluorinated products from nonselective reactions.
    • The remaining mass balance contained fluorinated products from nonselective reactions.
  • 49
    • 85130087924 scopus 로고    scopus 로고
    • see:
    • For reviews on photoinduced electron transfer (PET), see:.
  • 55
    • 85130089439 scopus 로고    scopus 로고
    • The identity of the base is not clear as there are three possible candidates: B8, 16, and bis(phenylsulfonyl)amide.
    • The identity of the base is not clear as there are three possible candidates: B8, 16, and bis(phenylsulfonyl)amide.
  • 58
    • 85130086462 scopus 로고    scopus 로고
    • As product 14 is relatively unstable, we primarily focused on the decarboxylation rather than the appearance of specific radical products.
    • As product 14 is relatively unstable, we primarily focused on the decarboxylation rather than the appearance of specific radical products.
  • 59
    • 85130086831 scopus 로고    scopus 로고
    • Whereas B7 and B8 are not mechanistically necessary as bases, in: sensitized photofluorodecarboxylations, the addition of these pyridine bases leads to the formation of fewer fluorinated byproducts with select substrates. See the Supporting Information for additional details.
    • Whereas B7 and B8 are not mechanistically necessary as bases, in: sensitized photofluorodecarboxylations, the addition of these pyridine bases leads to the formation of fewer fluorinated byproducts with select substrates. See the Supporting Information for additional details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.